Since going out on my own I have been putting off figuring out benefits due to excess cost and, let’s face it, it’s pretty boring stuff.

I finally sat down to take a look and get things sorted. Come to find out, it’s not as bad as I thought and there are some really great options out there.

I started by reading an article on some freelancing options. That was a good start, but I wanted some tips from people I know. So I polled my freelancing Twitter super-friends to see what they do. I got a mix of responses, ranging from:

• Live outside of the US
• Marry well
• Tell me when you figure it out
• Use an insurance broker
• Use eHealthInsurance

All great recommendations, but the last one was the most helpful. With it, I was able to find my option for Medical insurance — a high deductible policy with a health savings account (HSA).

I think what I ended up with is pretty cool, here’s why –

If I opted to continue my medical insurance through COBRA, it would have cost me just over $5,000 for the year. That’s even if I had no claims. And that number doesn’t include Dental or Vision.

With my new insurance policy?  Worst-case, I end up paying less (even with COBRA Dental and Vision included). Best case, I get a tax-sheltered interest bearing savings account to pay for my medical expenses that rolls over from year-to-year. And for each year I don’t reach my deductible in expenses is the lower it becomes (read: they reward being healthy).

Who knew such cool options existed? And who knew I would get excited about medical benefits? I for one am shocked.

What comes out is an unstructured representation of everything happening in my business — complete with a matching set of details. My mind calms, the clutching fear subsides, and I review what I’ve created. It’s extensive, detailed, daunting, and exciting — all at once.

This has happens every few days and has been going on for a couple of weeks. It’s not because I’m going crazy (I hope), but because I keep getting hit by flash floods of opportunity.

Here are the broad strokes from my manic moments — in aggregate:

• 2x – Prospective clients
• 2x – Existing clients
• 2x – Client partnerships
• 3x – Teaching engagements
• 3x – Meetups attending
• 2x – Meetups planning
• 4x – Books I’m Reading
• 3x – Additional offers to do consulting outside of my small business focus

I can’t obviously do all of this, but at least I have options. And it’s exciting to see things taking off.

I’ll let you know how it goes.

[Update: Make that 3x Existing clients. Just signed a prospect an hour after posting this!]

Failure is success if we learn from it.  – Malcolm Forbes

Hot on the heels of my…  recent education is something worth writing home about — my first success. Without the prior, I doubt the latter would have been as likely or as fruitful.

But really, I can’t take the credit. It’s my business partners and a great community that I have to thank.

A few months ago Arrgyle entered into an even-split business partnership with a hyper-local multimedia publication to create a spin-off, sister publication. The existing publication had already done the hard part, having amassed a large following for its area, garnering 20,000 unique monthly visits and netting close to six-figures in annual revenue. Pretty impressive for a single man covering the news of a small county.

He had a vision for the new publication and we helped him execute it. Primarily by helping set a content and marketing strategy, building out the site, implementing a new publishing workflow, developing ad pricing, and targeting clients for ad sales — all of this with an eye of launching on January 1st, 2012.

That day came and went, and here are the results so far:

• 20% of advertising inventory sold pre-launch
• Committed annual revenue of $19,800 (of which Arrgyle collects 50%)
• Over 3,000 unique visitors, spending an average of 4 minutes on the site
• A high percentage of new visitors daily
• Heaps of positive feedback from readers

So I really can’t get down about the results of my last project. It helped prepare me for this one. And ironically, the day after my last post I signed a new client that paid that day, received my monthly retainer from a client, and was wired the first installment of payment from SchuyLines — essentially covering my losses from the last project.

You know who you are. Even Steven! – Kramer

I have not failed. I’ve just found 10,000 ways that won’t work. — Thomas Edison

At the outset things seemed to make good sense — help an established small gift giving business of 15+ years sell their products online just in time for their busy season (the holidays). We cover tech & marketing expenses and they pay us with 25% of profit from the results.

Our decision to proceed was bolstered by the fact that they have strong margins, make at least 1/3 of their sales during the holiday season, and we had a 2 month window to work with.

So we jumped in with both feet — building them a graphically appealing website, taking high-end product photos, getting perfectly worded copy for product listings, doing targeted Facebook marketing, getting written up in and advertising on a popular local publication. And then we waited, watched usage data, and hoped for sales.

A few trickled in, but that was it. We got some user feedback, made some changes, and still saw the same results. We even worked up an alternative home page and tested it against the original. No dice.

All of this was transpiring as the small business owner was hit full-force by the retail boom of the season, leaving her incapacitated to work with us.

The holiday season came and went before we knew it and our numbers were less than spectacular. That is to say, Arrgyle spent more money that it earned, with ~$1,200.00 in expenses (not including our time) and $104.69 in revenue.

While part of me is bummed and a little freaked out, another part of me chuckles and chocks this up to a fairly inexpensive education. I learned so much in such a short amount of time and feel like no one could have taught me the insights I picked up by doing this. Or if they tried, I probably wouldn’t have listened.

The brick walls are not there to keep us out; the brick walls are there to give us a chance to show how badly we want something. — Randy Pausch

There are 3 elements to a successful startup founding team; Hacker, Hustler, and Designer — Paul Singh, co-founder of 500 Startups

Luckily for me, I found a business partner that helps me fill out Arrgyle’s missing roles.

I suffer from what I like to call “Rabid Inventor’s Syndrome” — I have lots of ideas. Some of them I even start to build. But then a new one comes along that is more interesting. When this happens I tend to leave the previous one behind, half-built, likely never to be touched again. Leaving it to gather dust on a shelf somewhere.

By working with a partner that overlaps into the “Hacker” realm with me, we share a common language, interest, and brain pattern. This enables me to share an idea, jam on it with someone that gets it, and see to it that we execute on it before a new idea comes along and steals our focus. Or, we realize it’s trash and throw it out.

And given our different backgrounds — we complement each other well. Me with my educational accomplishments and corporate experience, and him with his extensive hands-on industry experience.

Our partnership is not finalized yet, but it’s in process. His percentage of earnings from long-term client work is getting funneled in to his equity buy-in — which matches my initial cash outlay of $5,000. Once that triggers, he will be a 50% partner in the business.

We’re progressing there slowly, but it’s great motivation as we are starting to gain customer traction.